$141+ Cheap flights from Vermont to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Dec 5 — Dec 121
Round-trip
1 adult, Economy
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Find cheap flights from Vermont to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Vermont to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Vermont to ChicagoExplore the most affordable flight options available from Vermont to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2026.
Explore the most affordable flight options available from Vermont to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2026.
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:30 pm -
2 stops13h 16m
Sat 12/511:10 am -
Nonstop2h 24m
Deal found 10/31![United Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:15 pm -
1 stop23h 35m
Wed 12/304:59 pm -
2 stops22h 36m
Deal found 11/1![Multiple Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
Nonstop2h 51m
Mon 12/76:29 pm -
Nonstop2h 22m
Deal found 11/3![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/24:47 pm -
Nonstop2h 49m
Sat 12/54:37 pm -
1 stop5h 38m
Deal found 11/4![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:05 am -
Nonstop2h 59m
Mon 1/1811:00 am -
Nonstop2h 21m
Deal found 11/2![United Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:00 am -
Nonstop2h 59m
Fri 1/112:55 pm -
Nonstop2h 18m
Deal found 11/1![United Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:30 pm -
1 stop5h 31m
Sat 1/27:25 am -
Nonstop2h 20m
Deal found 11/2![United Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:55 am -
1 stop5h 51m
Sun 12/67:00 am -
Nonstop2h 17m
Deal found 11/4![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:25 pm -
2 stops7h 50m
Sun 12/66:00 am -
1 stop6h 33m
Deal found 11/3![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:05 am -
Nonstop2h 59m
Sat 1/169:00 am -
1 stop5h 44m
Deal found 11/2![United Airlines logo]()
$367
Best flights from Vermont to ChicagoDiscover carefully curated flight deals from Vermont to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 5, 2026.
Discover carefully curated flight deals from Vermont to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 5, 2026.
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:05 am -
Nonstop2h 59m
Sat 1/27:25 am -
Nonstop2h 20m
Deal found 11/4![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/205:50 am -
1 stop8h 30m
Mon 3/226:00 am -
1 stop6h 49m
Deal found 11/2![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/79:49 am -
1 stop5h 35m
Mon 1/116:28 pm -
Nonstop2h 23m
Deal found 11/1![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:05 am -
2 stops11h 01m
Mon 1/116:30 am -
1 stop7h 34m
Deal found 11/3![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:00 am -
Nonstop2h 59m
Fri 1/112:55 pm -
Nonstop2h 18m
Deal found 11/1![United Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
2 stops10h 57m
Sun 1/106:00 pm -
1 stop5h 27m
Deal found 11/3![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:50 am -
1 stop5h 33m
Mon 12/77:00 am -
1 stop5h 52m
Deal found 11/3![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/164:50 pm -
1 stop4h 42m
Mon 2/85:28 pm -
1 stop5h 10m
Deal found 11/3![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/810:40 am -
1 stop5h 37m
Tue 1/127:00 am -
1 stop5h 56m
Deal found 11/4![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:00 am -
1 stop6h 56m
Tue 1/121:45 pm -
2 stops9h 42m
Deal found 11/4![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:00 am -
2 stops8h 59m
Mon 11/232:44 pm -
2 stops8h 36m
Deal found 11/2![Delta logo]()
$389
Last-minute flights from Vermont to ChicagoDiscover last-minute flight deals from Vermont to Chicago. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Vermont to Chicago. Data last updated November 5, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
Nonstop2h 51m
Mon 12/76:29 pm -
Nonstop2h 22m
Deal found 11/3![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/24:47 pm -
Nonstop2h 49m
Sat 12/54:37 pm -
1 stop5h 38m
Deal found 11/4![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:30 pm -
2 stops13h 16m
Sat 12/511:10 am -
Nonstop2h 24m
Deal found 10/31![United Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:55 am -
1 stop5h 51m
Sun 12/67:00 am -
Nonstop2h 17m
Deal found 11/4![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:25 pm -
2 stops7h 50m
Sun 12/66:00 am -
1 stop6h 33m
Deal found 11/3![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:05 am -
Nonstop2h 59m
Mon 1/1811:00 am -
Nonstop2h 21m
Deal found 11/2![United Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:05 am -
Nonstop2h 59m
Sat 1/169:00 am -
1 stop5h 44m
Deal found 11/2![United Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:30 pm -
1 stop5h 31m
Sat 1/27:25 am -
Nonstop2h 20m
Deal found 11/2![United Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:15 pm -
1 stop23h 35m
Wed 12/304:59 pm -
2 stops22h 36m
Deal found 11/1![Multiple Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:00 am -
Nonstop2h 59m
Fri 1/112:55 pm -
Nonstop2h 18m
Deal found 11/1![United Airlines logo]()
$355
One-way flights from Vermont to ChicagoSearch for one-way flight options from Vermont to Chicago. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
Search for one-way flight options from Vermont to Chicago. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/155:15 pm -
2 stops22h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:15 pm -
1 stop23h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/175:15 pm -
1 stop23h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1312:32 pm -
2 stops32h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$176
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:09 pm -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:15 pm -
1 stop23h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:27 am -
3 stops30h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$188
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:03 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$205
Find flight deals from Vermont to Chicago
Keep the following information in mind while searching for Vermont to Chicago flight deals. Data was last updated November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $329 (United Airlines) |
One-way from | $141 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $389 |
Good round-trip deal | $435 or less |
Good one-way deal | $353 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Vermont to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 5, 2026.
Use the filters below to find and compare flights from Vermont to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Sat 3/6
7:00 am-12:44 pm
1 stop6h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$207
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Wed 12/9
11:58 am-6:30 pm
1 stop7h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$240
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Tue 11/10
8:40 am-4:10 pm
1 stop8h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$242
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Sat 12/19
6:05 am-8:04 am
Nonstop2h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$247
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Tue 12/29
6:00 am-7:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$247
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Fri 11/20
8:54 am-10:45 am
Nonstop2h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$249
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Sun 11/15
5:15 pm-6:45 pm
2 stops26h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$259
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Fri 11/20
5:02 am-11:44 am
1 stop7h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$259
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Sun 12/20
6:05 am-8:04 am
Nonstop2h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$277
BurlingtonChicago
BTV Burlington - ORD Chicago O'Hare Intl
BTVORD
Burlington
Wed 12/9
6:00 am-7:51 am
Nonstop2h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$281
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Vermont to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Vermont with our price prediction graph.
BTV-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Vermont to Chicago
USVT-CHI
BTV-ORD
What is the cheapest month to book a flight from Vermont to Chicago?
Currently, May is the cheapest month in which you can book a flight from Vermont to Chicago (average of $312). Flying from Vermont to Chicago in November is currently the most expensive (average of $452). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from VT to CHI?
Find hourly flight availability from Vermont to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 5, 2026.
One of the essential ways to save on airfare from Vermont to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 75% on airfare.
Weekly flight availability from Vermont to Chicago
Explore weekly flight availability from Vermont to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 5, 2026.
The most flights from USVT to CHI are scheduled on a Wednesday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Vermont to Chicago?
Airfare is typical for this route at the moment.
Vermont to Chicago flights typically cost between $319 and $514 in December.The cheapest round-trip price found within the last 5 days was $329 on United Airlines (Dec 4-Dec 5).
How far ahead should I book a flight from Vermont to Chicago?
Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Vermont to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Related info for your journey
Find useful and relevant information for your journey from Vermont to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Complete your trip
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Alternative routes for Vermont to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Vermont to Chicago by cabin class
Find flights from Vermont to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Vermont and Chicago flights
Browse other Vermont and Chicago flight options. Last updated on November 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Vermont to Chicago flights
Consider these flights traveling from Vermont to Chicago.
Top 2 airlines flying from Vermont to Chicago
Discover the top 2 airlines that operate flights from Vermont to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$239 | Average$339 | FlexibilityNo cancel fee | On-time71% |